But instead of uniting fans, the concert quickly became the centre of a global debate about politics, free speech and the limits of artistic expression. Bet Ed Sheeran expected his Loop tour to make headlines, but not in this particular way.

But that's exactly what happened.

Macklemore, whose real name is Ben Haggerty, has been a vocal supporter of Palestine since this conflict began in 2023. He has used his music, social media and public appearances to call for a ceasefire and an end to what he describes as the oppression of Palestinians.

His 2024 song “Hind’s Hall” is named for the building Columbia University protesters occupied and renamed in memory of five-year-old Palestinian girl Hind Rajab. He has subsequently released “Hind's Hall 2” since then. Aside from the music, he has also donated medical equipment to Palestine.

Now, on September 4, 2026, Macklemore mounted the stage at Ed Sheeran's Loop tour in New Jersey and further publicised his position by saying the words, "free Palestine ". This did not sit well with people like Robert Kraft, owner of Gillette Stadium and the New England Patriots, and Pink. According to these two, Macklemore's words on stage were anti-semitic.

According to a statement posted on Macklemore's social media handles, Ed Sheeran informed him that Kraft has given him an ultimatum, it is either Macklemore is removed as an opening act, or he will not be given Gillette Stadium to perform because he does not want to see him there. It did not end there, other venue owners also joined with Kraft, giving Ed Sheeran that same ultimatum: "drop him, or say bye to our venues.

That is how Macklemore got dropped by Ed Sheeran. Following this, other opening acts like Lukas Graham, Aaron Rowe, Finneas, and even Ed's backing band, Beoga, all withdrew from the tour in solidarity with Macklemore, so that artists should be able to freely express themselves without being intimidated.

What makes this even harder to explain away is that Ed Sheeran has done this before and done it loudly.

Back in March 2022, weeks into Russia's invasion, Sheeran didn't hesitate to pick a side. He performed at the Concert for Ukraine in Birmingham, telling the crowd it was "such an important cause" and that he was "honoured to be here," having just shot a music video in Kyiv months earlier. That single concert raised over £13 million for Ukrainian humanitarian relief. Nobody told him Ukraine was "too political" for a stage. No venue owner issued an ultimatum. No promoter pulled the plug. Sheeran stood in front of a stadium waving Ukrainian flags, and it made him look compassionate, not controversial. He even remixed his song Two Piece with a Ukrainian band.

So why is Palestine different?

Ms Rachel, the children's YouTuber turned pro-Palestinian voice, asked it directly, accusing Sheeran of showing up for Ukraine while treating Palestine as "too dangerous and political" to touch. And it's worth sitting with, because Ukraine had two sides too.

There was an aggressor and a country under siege, and Sheeran chose the side of the people being bombed without a second thought. Nobody demanded "neutrality" from him then. Nobody asked him to consider "both sides" of an invasion. So what changed between 2022 and 2026? Is it the war itself, or the amount of power standing behind the side asking for silence?

It's also worth noticing what happened after Ukraine: nothing. Sheeran didn't take another public stance on a war again, didn't lend his stage to another humanitarian appeal, until Macklemore forced the question onto it in September 2026. Four years of silence on conflict, sandwiched between one very visible act of solidarity and one very visible act of distancing. Is that genuine uncertainty about a more contested conflict in a sense that he simply doesn't know which "side" to back? Or did something happen after Ukraine that taught him which wars are safe to touch and which ones cost you stadiums, sponsors and headlines? We don't know. But the pattern itself is the story: solidarity for Ukraine came easily and cheaply; solidarity for Palestine, once it actually arrived on his stage uninvited, had to be managed, contained and eventually priced out in donations instead.

Because that's what the money at the centre of this now looks like, a price tag. Once Macklemore announced he'd give the full $1 million he earned from the tour to Palestinian relief organisations and challenged Kraft to match it, Kraft didn't just match him, Sheeran had already quietly committed $2 million of his own, and Kraft matched that instead, bringing the total from the two of them to $4 million, on top of Macklemore's $1 million. Suddenly there's $5 million moving toward Gaza. The donation reads less like conscience and more like reputation management, especially for Kraft.

And that brings us back to the most basic question in this entire saga: what was Ed Sheeran thinking when he booked Macklemore in the first place?

This isn't a case of an artist getting radicalised mid-tour. Macklemore's position on Palestine has been public, loud and consistent since the war began in 2023. He's got "Hind's Hall," the donations, the UNRWA proceeds, the "Hind's Hall 2" follow-up, the Seattle festival appearances. Anyone booking him in 2026 knew exactly who they were putting on that stage. So either Sheeran genuinely didn't expect Macklemore to bring that same conviction to a Loop Tour date in New Jersey, or he did not mind it until it threatened his tour venues. If it's the latter, that says something on its own: that even an artist as visibly, unapologetically pro-Palestine as Macklemore was still expected to perform quietly, and only got "too political" the moment he refused to.

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